N,N-Dimethylaniline → HCID 21077807, compound

HRID 468550Notes

Reaction equation

HRID 468550 reaction equation
P(Cl)(Cl)([Cl:3])=O.CN(C)C1C=CC=CC=1.[CH3:15][O:16][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[N:23]=[N:22][CH:21]=[C:20]2O>>[CH3:15][O:16][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[N:23]=[N:22][CH:21]=[C:20]2[Cl:3]

Participants

4

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 178488188HCID 178488188, compound

Product 1

HCID 21077807HCID 21077807, compoundYield 59%

Procedure

Phosphorous oxychloride (5 ml) was added to a mix of dimethylaniline (157 mg, 1.3 mmol) and 6-methoxy-4-hydroxycinnoline (208 mg, 1.2 mmol). The reaction was heated at reflux for 15 min, then cooled and concentrated under vacuum. The residue was partitioned between chloroform (100 ml) and water (30 ml), then the organic layer was washed with brine and dried (Na2SO4). Chromatography of the residue adsorbed onto silica gel (3 g) on silica gel (15 g) eluent CH2Cl2 to 10% Ethylacetate/CH2Cl2 gave 6-methoxy-4-chlorocinnoline (135 mg, 0.7 mmol) in 59% yield as white yellow solid. δH (CDCl3)=4.03 (s, 3H); 7.28 (d, 1H); 7.51 (dd, 1H); 8.41 (d, 1H) and 9.22 (br s, 1H). MS (ESI) (M+H)+ 195.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 15 min
  3. temperaturecooled
  4. concentrationconcentrated under vacuum
  5. customThe residue was partitioned between chloroform (100 ml) and water (30 ml)
  6. washthe organic layer was washed with brine
  7. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-3deddce038244eaabcde88f473fe8b85
Source dataset
uspto-grants-2014_01
Patent number
US08624025B2

Reaction notes

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